Book Holiday Homes in Middleburg

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Featured Holiday Homes in Middleburg

Breathtaking views  with an  indoor private pool, come escape with us

Breathtaking views with an indoor private pool, come escape with us

Bluemont
Stay at this vacation home in Bluemont. Enjoy private pools, a fitness center, and a garden. Our guests praise the pool and the helpful staff in our reviews. ...
Breathtaking views with an indoor private pool, come escape with us
Cozy townhome with WiFi and AC in charming Sterling

Cozy townhome with WiFi and AC in charming Sterling

Sterling
The price is NZ$210 per night from 24 Dec to 25 Dec
NZ$210
includes taxes & fees
24 Dec - 25 Dec
Stay at this vacation home in Sterling. Enjoy an in-room coffeemaker, in-room fireplaces, and air conditioning. Popular attractions Reston Town Center and Grand ...
Cozy townhome with WiFi and AC in charming Sterling
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
The price is NZ$1,133 per night from 26 Dec to 27 Dec
NZ$1,133
includes taxes & fees
26 Dec - 27 Dec
Book a stay at this family-friendly vacation home in Charles Town. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Hollywood Casino ...
Terra Alta - Incredible River Views and Hot Tub!
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Charles Town Home w/ Private Pool & Hot Tub

Charles Town Home w/ Private Pool & Hot Tub

Charles Town
Book a stay at this family-friendly vacation home in Charles Town. Enjoy private pools, patios, and cable/satellite TV service. Popular attractions Hollywood ...
Charles Town Home w/ Private Pool & Hot Tub
 Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!

Marshall
Book a stay at this business-friendly vacation home in Marshall. Enjoy free WiFi, a garden, and concierge services. Popular attractions Upperville Park and Glenwood ...
Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated  Sunny Luxurious Indoor

YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor

Middleburg
Stay at this vacation home in Middleburg. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Greenhill Winery & Vineyards and Red Fox ...
YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor
Cozy Entire Guest Suite by IAD Intl. Airport

Cozy Entire Guest Suite by IAD Intl. Airport

Herndon
The price is NZ$280 per night from 5 Jan to 6 Jan
NZ$280
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Herndon. Enjoy air conditioning. Popular attractions Reston Town Center and Frying Pan Farm Park are located nearby.
Cozy Entire Guest Suite by IAD Intl. Airport
The PINK PEARL in Historic Leesburg

The PINK PEARL in Historic Leesburg

Leesburg
Stay at this vacation home in Leesburg. Enjoy free WiFi, a garden, and patios. Popular attractions Raflo Park and Gleedsville Art Gallery are located ...
The PINK PEARL in Historic Leesburg
Stunning House! Minutes From Shenandoah River

Stunning House! Minutes From Shenandoah River

Harpers Ferry
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, a garden, and patios. Popular attractions Hollywood Casino at Charles Town Races and Shenandoah ...
Stunning House! Minutes From Shenandoah River
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Middleburg Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middleburg vacation homes are the perfect way for you to wing it.

Holiday houses in Middleburg let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middleburg in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middleburg adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middleburg with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middleburg vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middleburg Holiday Homes essential information

Accommodation
244 Holiday Homes
Lowest Price
NZ$153
Highest Price
NZ$1,272
Popular accommodation
Breathtaking views with an indoor private pool, come escape with us, Cozy townhome with WiFi and AC in charming Sterling, Terra Alta - Incredible River Views and Hot Tub!, Charles Town Home w/ Private Pool & Hot Tub, Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!, YELLOWWOOD COTTAGE - Private Outdoor Space Sophisticated Sunny Luxurious Indoor, Cozy Entire Guest Suite by IAD Intl. Airport, The PINK PEARL in Historic Leesburg, Stunning House! Minutes From Shenandoah River

Top trending hotels in Middleburg

Salamander Resort And Spa

Salamander Resort And Spa

5 out of 5
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is NZ$1,272 per night from 1 Jan to 2 Jan
NZ$1,272
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 5-star luxury resort in Middleburg. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Red Fox Fine Art and Museum of ...
Salamander Resort And Spa
The Red Fox Inn & Tavern

The Red Fox Inn & Tavern

4 out of 5
2 E Washington St, Middleburg, VA
The price is NZ$654 per night from 2 Jan to 3 Jan
NZ$654
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this 4-star inn in Middleburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Red Fox Inn & Tavern
Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
2300 Dulles Corner Blvd, Herndon, VA
Fully refundable
The price is NZ$198 per night from 5 Jan to 6 Jan
NZ$198
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this golf hotel in Herndon. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean ...
Hyatt Regency Dulles
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Best Western Dulles Airport Inn

Best Western Dulles Airport Inn

2.5 out of 5
45440 Holiday Drive, Sterling, VA
Fully refundableReserve now, pay when you stay
The price is NZ$153 per night from 25 Dec to 26 Dec
NZ$153
includes taxes & fees
25 Dec - 26 Dec
Book a stay at this business-friendly hotel in Sterling. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Dulles Airport Inn
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See all available properties in Middleburg
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.